Indole → 9-Methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-beta-carboline-2-carboxylic acid tert-butyl ester

HRID 6747Notes

Reaction equation

HRID 6747 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:16]=3)[NH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:32]C(C)([O-])C.[K+].C1OCCOCCOCCOCCOCCOC1.IC.N1C2C(=CC=CC=2)C=C1>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:21][Si:22]([CH:23]([CH3:24])[CH3:25])([CH:26]([CH3:28])[CH3:27])[CH:29]([CH3:31])[CH3:30])[CH:16]=3)[N:11]([CH3:32])[C:10]=2[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 5

HCID 798IndoleHCID 6328Methyl iodideHCID 2855718-Crown-6HCID 23544277HCID 23544277, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 235442769-Methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-beta-carboline-2-carboxylic acid tert-butyl esterYield 41.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

A solution of 6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (175 mg, 0.39 mmol) in 3 mL of ethyl ether was added to a vigorously stirring solution of potassium tert-butoxide (263 mg) and 18-crown-6 (16 mg) in 10 mL ethyl ether. After 10 min, iodomethane (73 uL) in 0.5 mL of ethyl ether was added to the indole solution and the resulting mixture was stirred for 2 h. The solids were removed by filtration and the solvent was evaporated. Silica gel chromatography (10% ethyl acetate in hexanes) gave 9-methyl-6-triisopropylsilanyloxy-1,3,4,9-tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (75 mg).

Workup

  1. customThe solids were removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b5ef23cd1e7d40e5b80f3c58363f7221
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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